Cycling the Heel of Italy - Alberobello to Lecce

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Well organised and efficient. Good quality bikes.

Mr Exley, 28 Apr 2025

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Well organised, good communication pre holiday, friendly team

Mrs Leslie, 12 Oct 2024

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This is my second Headwater cycle holiday and they never fail to deliver an exceptional experience. All went like clockwork the organisation and hotel selection perfect

Mr Bryant, 2 Oct 2024

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Loved the trip. It was super easy to get around and was exactly what I was hoping for.

Mrs Jones, 14 Sep 2024

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Had a great holiday in Puglia with Headwater. Accommodation was good to excellent in some cases and the app really easy to use. Met other lovely people en route. Would definitely travel again . Airport transfers are better organised locally though as much cheaper.

A Valued Customer, 13 Sep 2024

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The transportation of cases between hotels and the cycling App were excellent. Hotels chosen on the whole have been in good locations

A Valued Customer, 11 Sep 2024

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Really well organised.

A Valued Customer, 9 Sep 2024

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We thoroughly enjoyed our weeks cycling the heel of Italy, The Headwater navigation App was excellent and made each days cycling worry free. The organisation from start to finish was very well done.

Paul Lelliott, 23 May 2024

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We had a great time in Italy and enjoyed the route and variation of the area. Is not a cheap holiday and after the physical challenge of the day expect a certain standard of accommodation for the night which we had. We had an exceptional rep. in Croatia last year, felt a bit different this time round, welcome meeting about the bikes out in the street, didn't feel very personal, language was a bit sketchy also. There was a road closure in Alberobello which meant we had to walk quite a way with our luggage which made us late for the welcome briefing which didn't help but was out of our hands.

Margaret Down, 23 May 2024

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Really great holiday. The app is fantastic. Concerns about getting lost or stressed with route finding were irrelevant.

Anne-marie Furse, 16 May 2024

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We hadn’t used the navigation app before but it was so easy to use. Had a few little blips with it in towns but soon got the hang of it. The rides were about 35-40 miles a day, four of the days were easy. The other two days had some long and sneaky climbs. We were the only ones at the hotel stops not on e-bikes though.

The hotels were all comfortable and easy to find. The masseria stay was lovely. Food in Puglia is excellent especially if you love fish and seafood. Might be a bit limiting if you don’t. The wine is pretty good too.

Quite a lot of variation on the route as you ride past trulli, along the coast and through vineyards and olive groves. Sadly the litter and fly tipping along the route, especially the Ionian coast, is dreadful.

Christine Thomas, 13 May 2024

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Cycling the Heel of Italy was a fabulous trip with an excellent itinerary and lovely choice of hotels exploring beautiful undiscovered Puglia. We went in early May & the wildflowers were everywhere, just wonderful and weather was perfect as sunny & hot but not too hot. Very few tourists so it was lovely and quiet! The route choices were excellent, taking us directly to fabulous view points or things of interest, we particularly enjoyed the strade bianchi off road parts though these are few as the route was mainly quiet lanes with few cars, drivers are in any case very courteous to cyclists. We are keen cyclists at home and are fit so were fine with the occasional slightly hillier days, views on those days were so beautiful, but most days were really fairly flat. Scenery was so varied with many olive groves, wild flower meadows, beautiful quiet sandy beaches for impromptu swims en route, then more rugged coastlines with rocks and sea caves. You get to see the real Puglia which is just so beautiful. The locals were incredibly friendly and kind to us. The bikes were hybrids and simple/comfortable. The local cuisine is delicious, with lots of fresh seafood. Many interesting villages to stop and explore en route for coffee, local cakes, ice creams, or Puccia for lunch. So much history, beautiful towns/villages, old churches, castles. We finished in Lecce which really is truly stunning so make sure you allow enough time to fully explore it! A wonderful holiday thank you Headwater.

Susannah Pink, 5 May 2024

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It was great and we would definitely like to do another cycling holiday with Headwater

Deborah Meech, 4 May 2024

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We have previously done multiple holidays (cycling and walking) with Inntravel, as we like their service, use of small hotels and quality routes. We went with Headwater this time as we couldn’t find an Inntravel holiday we fancied that was running at this time (that we hadn’t done already!) I’m pleased to say Headwater met the standard we were hoping for. The route app was excellent, and apart from the some sections of the coast road, felt very safe and enjoyable.
Although we were at the start of the season, we managed to find places for coffee, lunch and ice-cream each day, which was good.


Rachel Helen Haigh, 28 Mar 2024

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Overall, a fantastic, well managed holiday. Highly recommended.

Sarah Louise Marr, 25 Mar 2024

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I was extremely pleased with this holiday. I travelled early in the season (pre-Easter). There were good traffic-free sections, but in fact all the roads, even the main ones, were unbelievably quiet. You do have to understand that at this time practically everything is closed, sometimes entire small villages. On the other hand, it was even possible to cycle round the narrow medieval streets, which I imagine is not easy in the season. The routes chosen were ideal, scenic, quiet; I could not fault anything. While there are some beautiful cycle lanes, some of the road surfaces. especially in the country, are challenging, and there are good potholes. Be prepared for distressing levels of fly-tipping, even in some very rural areas.



Martin Wyatt, 21 Mar 2024

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Really well organised. Felt confident with all arrangements. Slight hiccough at the end when our itinerary said depart hotel for Bari at 1000 when it should have been 0900 but all ended well.

Kentigern Haworth, 8 Oct 2023

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This trip was really fun and well organised. Would recommend

Pamela Tilt, 5 Oct 2023

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A fantastic holiday in a beautiful part of Italy. The locations each night were really varied from amazing farmhouse in the country to modern hotel overlooking the harbour.

Cycling varied from coast road to cycling through olive groves. Would definitely recommend.

Mark Baseley, 2 Oct 2023

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We had a great holiday in Puglia. The countryside was lovely (except for the appalling litter problem which seems to blight southern Italy and Sicily), the towns were stunning and the length of cycling days just about perfect. The hotels were generally good, and the Masseria Bosco was outstanding. Swimming in warm seas on both sides of the region was very special, as were the gelati! The navigation app was brilliant - you really can't get lost (though you do have to be a bit careful in busy cities) and Headwater's communication was excellent.

Elizabeth Douglas, 26 Sep 2023

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We really enjoyed the route and accommodation, and felt we had seen so much of Puglia. The route is difficult to get to and from, but fortunately we have some friends who live in Puglia, so they picked us up from Brindisi airport, we stayed with them for a few days and then they drove us to Alberobello. I discovered, whilst we were there, we could have got back from Lecce to Brindisi by rail to meet the Sunday flight. Instead we had to rely on staying with our friends again for a few nights). This would have been very useful information to have upfront when planning a trip, and this is where Headwater are weak. You should be giving more information on how to get to places, from different uk airports, rather than just via the London airports. I think you’d get more customers (as we were surprised that we were the only two on this trip).

Stephen Eatwell, 17 Sep 2023

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Very positive. The Puglia itinerary was excellent. The scenery was very varied: inland (vineyards, olive groves), beaches on the coast and cliffs on the coast. We visited some lovely towns / villages in Puglia and had the time to see them each day. Most of the roads were not too busy. The navigation app was superb at directing us.

Patrick Strafford, 22 Jun 2023

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Cycling holiday with Headwater was excellent and I would recommend this trip. We enjoyed the change of scenery from the inland routes of the first two days to the beautiful coastal routes of days 3, 4 and 5 - we spent two afternoons on the beaches which were outstanding. The trip have everything you need. The hotel in Gallipoli was only average but the remainder were very good. The family run hotel in Avetrana with a swimming pool was very special - staff amazing. We also loved the Hotel in Otranto where the staff were again great, the room was lovely and breakfast amazing with lots of choice. Overall the cycling was pleasant, not too challenging and a great way to see Italy. We will look to do similar holidays with Headwater and have recommended this to friends.

MAYHEW, 5 Jun 2023

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This tour around Puglia offers a varied insight into the region from the Trulli houses to resort hotels. Food and wine are consistently excellent and the hotel accommodation overall exceeded our expectations. The cycling, for the most part, is enjoyable. I would caveat that by saying some of the coastal roads are busy, even at the end of May/beginning of June and despite assurances from Antonio at the start of the tour that Italians treated cyclists with a degree of courtesy we found this to be generally not the case.

LUCAS, 29 May 2023

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The cycling was fun and the app was generally easy to use though you should take an external battery pack. My phone was 3 years old and you need to set the screen to be quite bright so it uses up power quite quickly. The hotels that we used were all 3* but were comfortable. All hotels provided excellent breakfasts. We went in early May which is described as part of the holiday season but we found most places still closed so stopping off along the way wasn't as easy as we expected. One thing that we were really surprised by was the cost of transfers to and from the airport that Headwater wished to charge. Something like �240 from Bari to Arborobella (we caught a bus for 8 euros, and over �400 from Lecce back to Bari ( we caught the train for 24 euros). We hadn't been cycling for some years before booking this holiday but we practised for 5 weeks before going and we were fine.

Mrs REDSHAW, 6 May 2023

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Excellent. Superb trip, well organised.

Ms Turner, 8 Apr 2023

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Itinerary fine. Unfortunately weather not great do not a lot to do when cycling finished

Mr Mitchell, 3 Apr 2023

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Super. Cycling tour. Everything we needed was provided by friendly and efficient service. Highly recommended.

Mrs Butler, 11 Sep 2022

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A great active holiday where you travel through different landscapes to arrive in interesting towns with lovely hotels.

Mrs Kennedy, 27 Jun 2022

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Great route. Varying quality of hotels. Poor bikes. Expensive for what we got.

Mr Scott, 21 Jun 2022

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A very enjoyable holiday, staying at interesting places in good accommodation. We would certainly book with Headwater again for a cycling holiday

Mr Rhodes, 22 May 2022

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It was lovely to arrive at the end of a ride in the little towns of Puglia, all different and charming. Some of the cycling was really spectacular, particularly along the coast. I was pleased to have an e-bike as the temperature was way over 30 degrees everyday at the end of May. As someone not very tech-savvy, I needed help with the navigation app. Remember to download last-minute adjustments just before you go!

Ms Hall, 21 May 2022

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A great itinerary, a lot of variation in level of challenge.

Mrs Haddock, 16 May 2022

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This cycling route through Puglia is a stunningly beautiful one - particularly in late May when the poppies and other wild flowers were in full bloom; the weather warm but not scorching and not too busy with other tourists. This was the first Headwater cycling trip I have done without 'stay put' days, and the overall mileage each day (at leisurely pace) did mean there was little spare time for sightseeing. However, it was absolutely worth the effort to visit each of the locations - they were wonderfully varied and I wouldn't have wanted to miss out on any of them!

One of the days involves taking a train - it's worth noting that not all the trains allow bikes, and we were lucky to have had help lifting up the bikes into the hanging racks on the train - a tricky manouevre for the vertically challenged!

Mrs Davidson, 14 May 2022

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Fantastic way to see the glorious countryside, towns, cities and natural beauty of Puglia. Well organised, good bikes, good accommodation and we think the best way to immerse yourself in a location. As firstimers with Headwater would highly recommend to anyone.

Mr Becket, 8 May 2022

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Excellent. the App was easy to use for middle aged people who usually ask their children to work this kind of thing out. The Headwater emails were well timed and informative and when you passed us on to Gulia cycle tours, they were equally as efficient. The route was fantastic, the hotels just ideal for this holiday. The people we met from Puglia Tours delightful. We had 2 potentially big problems - A) one of our parties' bags didn't arrive from England on our flight. So we logged a missing bag form at Barri airport but it was difficult with language barrier and not knowing where we would be if and when the bag might catch up with us. Headwater were amazing and the bag caught us up 2 days later. And the driver from Puglio Tours took us from Barri airport to a hypermarket ( thank god open on a Sunday pm) to buy essentials. We also had a problem with a bike and again - fantastic backup and all sorted. Best holiday & when probs occurred the finest back up

Mrs Dudgeon, 8 May 2022

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An exceptional route - everything had been thought of. The first day is a long distance so it might be off putting for those who don’t cycle long distances regularly. The food everywhere is of a fantastically high standard. We recommend Le Bubbole in Matera, La Cantina in Alberobello and The Dish in Ostuni. Booking in advance recommended.

Mr Hrouda, 3 Apr 2022

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Our holiday was a celebration for our 30th wedding anniversary. In order to be consistent with the previous thirty years of marriage I left the planning until the last minute. I contacted Headwaters barely two weeks before the half term started yet they were able , as ever, to provide a first class service which totally met what we were looking for. From the moment we landed, where we met Mimmo our agent, until our departure from our gorgeous Lecce hotel on the final morning, we encountered nothing but an amazing service wherever we visited or stayed. We loved all of the accommodation as well as the stunning routes. Puglia is indeed an astonishingly beautiful region in Italy, as evidenced by the breath taking coastal routes to Gallipoli and Otranto. Likewise the climb to the hilltop town of Ostuni, as well the town itself, was simply stunning. I am running out of synonyms for brilliant but that is the adjective that I want to use to describe the everything about the trip. Thank you.

Mr WADE, 24 Oct 2021

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It was a well thought-out itinerary which took in the high-lights of Puglia - rural rides to beautiful hill-top towns and coastal rides with lovely views over the Mediterranean.

Mr HALL, 26 Sep 2021

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Excellent holiday with good hotels, great scenery and realistic riding days for the described activity level. The bikes were excellent and comfortable.

Mr Paul, 19 Oct 2019

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This was our first cycling holiday (we are in our seventies) We had the most enjoyable time, meeting up with fellow cyclist from other countries on route

The towns we stayed in and the hotel were all very good. The cycling was almost all on quiet roads. We would certainly like to book another trip. Mary and Tim



Mr Partridge, 5 Oct 2019